A transition metal complex which has an optically active diphosphine compound as a ligand is very useful as a catalyst for an asymmetric reaction, and until now many catalysts have been developed.
Among the catalysts, in combination of a base compound, a ruthenium-diphosphine-diamine complex is known as a highly active catalyst for an asymmetric hydrogenation (for example, PLT 1). As a method for synthesizing the complex, [RuCl2(p-cymene)]2 as a precursor of the complex reacted with an optically active diphosphine and an optically active diamine in order in a specific solvent is known (PLT 2), as an example. In addition, as a complex having an optically active diphosphine and a tridentate amine ligand, the compound represented by the following formula is known (PLT 3).

The ruthenium metal complex having an optically active diphosphine compound and a diamine compound as a ligand is highly useful because of the use for asymmetric hydrogenation of various carbonyl compounds, showing a high activity and high enantioselectivity, and giving an optically active alcohol compound with high optical purity. However, such catalyst shows high performance but not for every carbonyl compound, then development of a catalyst with higher activity is needed.